At long last, Southwest Airlines has announced information and updated dates regarding their new service to Hawaii.

Service from Oakland to Oahu, Maui and Kona from $49 Each Way!

Initial service to Hawaii begins on March 17, 2019 from Oakland and San Jose to Maui and Honolulu. From first look and some great research done by Frequent Miler, we see that fares are starting as low as $49 or 1,950 Rapid Rewards points!

Some of the lowest priced options are no longer available since word first got out. If you are looking for travel later in the year, there are still deals to be had, especially if you take into consideration the benefits of booking with a Companion Pass and getting 2 free checked bags.

Service from San Jose to Begin in May

Service from San Jose to Honolulu will begin on May 5, 2019. Service to Kona begins on May 12, 2019. For those looking to travel to Maui, that route starts service on May 26, 2019.

Southwest Airlines Inter-Island Hawaii Service

Taking advantage of Southwest Airlines’ unique Point-to-Point Flying strategy, they can offer better pricing on inter-island flights as much as they can on routes from the mainland.

With initial pricing as low as $29 or 1,329 Rapid Rewards points, Southwest is competing head to head with limited options that ofter cost $100 or more. Inter-island service will begin May 12, 2019.

Traveling to Hawaii from Chicago (MDW) and Baltimore (BWI)

Speaking of their “Point to Point” network, you might be curious as to how much it will cost you to get to Hawaii if you’re not originating in one of the five California markets. For those who are flying out from one of Southwest’s larger “hubs”, there are connecting itineraries from Chicago and Baltimore beginning the second week of April.

One way out-bound fares look to be as cheap as $162 or just 9,392 Rapid Rewards points!

Be careful, however, as Frequent Miler points out, there are some difficulties in booking return itineraries. While you might have luck booking these on the phone, you may also just want to book separate flights to take advantage of timing for these cheap flights.

Prices appear to jump a bit during July, but drop again once you start to look for flight options through Fall 2019.

Southwest Airlines Heads to Hawaii: The Fine Print

Pricing has been fluctuating since the announcement mainly from all the pent up anticipation regarding this news. If you weren’t able to get some of the prices that were quoted as of this morning (3/4/19), be sure to check back often. When it comes to booking with Southwest Airlines, because any available seat can be used for either award or Companion Pass bookings, availability will more than likely open up as others cancel or finalize plans.

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